


Four People Ruby Seduced & One She Actually Fell For (Or: Ruby's Epic Love Affair with Humanity in General and Sam in Specific)

by tuesday



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Canon, F/F, F/M, five things
Language: English
Status: Completed
Published: 2010-03-24
Updated: 2010-03-24
Packaged: 2017-10-08 06:53:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,762
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/73894
Author URL: https://archiveofourown.org/users/tuesday/pseuds/tuesday
Summary: <blockquote class="userstuff">
              <p>In which Ruby has a lot of sex, is not any kind of therapist that would be legal, and helps a few people out for her own reasons.  (S4/S5 AU)</p>
            </blockquote>





	Four People Ruby Seduced & One She Actually Fell For (Or: Ruby's Epic Love Affair with Humanity in General and Sam in Specific)

**Author's Note:**

> Thank you so much to jmtorres for betaing and audiencing bits and basically enabling my Ruby love and thank you also to wanlorn for letting me babble happily about Jo. This is AU for the end of S4 and much of S5 (but with some events repeating) and is of the school of: just roll with it. For that price of admission, you get Ruby/Jo! (Not to mention a fuck ton of other Ruby pairings.)

1\. The Mark: Castiel, Angel of the Lord

Castiel might have been an angel of the Lord, but Ruby was the best fucking demon in Hell or out of it. Also, this body was incredibly hot, if she did say so herself. She was so pleased with it that she smoothed her hands down her hips in a mostly automatic gesture of her joy and pleasure, much like she'd seen Dean smooth a hand across the hood of his car. Castiel tilted his head.

"If you're attempting to seduce me, you will have to try harder than that. I see you as you truly are." His voice was mostly puzzled, and Ruby grinned. She hadn't intended anything of the sort, but now that she thought about it and Castiel had revealed himself to be something of a soft touch--or at least someone who wasn't planning to immediately burn her from her host given the slightest provocation--it sounded kind of like fun.

"We'll see about that." Her grin transformed into something of a smirk. "And who said anything about _trying_?"

Sam and Dean tumbled in the door, mid-argument about something--likely who was going to get first shot at the first aid kit judging by the way Sam's forehead was bleeding and how Dean was holding his left arm--and came to an abrupt stop. Their stares went from one to the other, and back again. Sam's ended on Ruby with an "Are you okay?" stare, and Dean's on Castiel's like he was asking, "Why didn't you smite her while you still had the chance?"

Dean was taking a while to come around to her charm. Ruby gave him another month before he fell into bed with her. It would be fabulous, angry sex filled with delicious self-loathing and conflicted thoughts (on his part; Ruby had no illusions about what she wanted and saw no moral conflict in taking it). Ruby gave it another several weeks after that for Dean to finally catch on that she and Sam were in a _very_ open relationship and both were availing themselves of the opportunities that presented. Her only regret was that the likelihood of snagging both at the same time was so low as to be invisible even from the deeper pits of Hell. (Ruby would know.)

"Aw, baby, did you come home for me to kiss it better?" Ruby asked, smirking at Dean's unimpressed expression and grabbing a hand towel to press to Sam's head.

Sam hissed at the pressure and said, "If it's all the same, I'd prefer some ice." Then, with the sudden horror of a boyfriend expecting to sleep on the couch--never mind the closest approximation the motel had was a single chair with crooked legs and dark, suspicious stains and that it was Sam and Dean's motel room in the first place--"Not that your kisses aren't great. Because they are. But--"

"Easy," Ruby said. "We can do the relationship mind-fucking later. Right now, I'm going to make you an ice pack." Because Ruby was awesome, she snagged the ice bucket and did so. Because she was downright _amazing_, she managed to brush up against Dean _and_ squeeze an ever unimpressed angel's ass on the way out.

For a while, it became something of a joke. Ruby hit on the angel, the angel looked long-suffering, Dean made some furious faces and demanded to know Ruby's intentions ("To have fun," didn't seem to cut it with Dean), and Sam, as with most of Ruby's other hook-ups, stayed well out of it. There were some ups and downs, a few minor setbacks--the dead Lilith and Lucifer rising thing, Castiel getting blown to tiny bits by an archangel, Sam trying to dump her along with his brother when he went on his "no demon blood and no more hunting" kick--but overall, Ruby apparently had some sort of effect, because when Castiel failed at hooking up with a prostitute (and Ruby could've told Dean how well _that_ was going to go over), he turned to Ruby in his time of need.

Well, okay, more like Ruby happened to be around afterward when Castiel was, at Dean's insistence, relaying the story to Sam, and she continued to stick around after the boys went to bed--humans and their petty need for sleep--to suss out more details that might have been left out for Sam's benefit. "So did you fuck him yet?" Ruby asked.

"I don't understand," Castiel said carefully.

"Dean," Ruby said, pulling Castiel further from the hotel room door to settle against the Impala. She imagined Dean's face if he found them there, sitting on the hood, and it sent warm fuzzies curling 'round her heart. "You said he promised he wouldn't let you die a virgin. So he totally popped that cherry, right?"

"I didn't die," Castiel said in that same careful tone, "and thus he has kept his promise."

"That's not the type of promise that goes _away_," Ruby said. "It's the type of promise you _fulfill_."

Castiel looked doubtful, but in the way that said he didn't want to believe her and yet totally did. That was good, because Ruby wasn't actually lying. Dean Winchester definitely would want to keep his promise. Just--probably not in the way Ruby intended. Ruby pictured his face in reaction to this, and that was even better than the image elicited by sitting on the Impala and scuffing the paint job.

"I'm sure we could find you another brothel," Ruby said, doing her best to look helpful.

"It would end the same way," Castiel said, and his expression was the angelic equivalent of glum, lips turned down the slightest bit.

"It's a good thing you've got another option," Ruby said. Castiel stared at her blankly. "Me," Ruby clarified.

"No," Castiel said, then added belatedly, like he'd been listening to Sam's lectures on manners lately, "thank you."

"It's an open offer," Ruby said.

"That I refuse," Castiel said.

"Did I mention it's one that won't get you slapped no matter what you say in a moment of ill-advised honesty _and_ comes complete with whatever kinky shit your little rebellious angel heart might like to try on for size?" Ruby showed her teeth in something like a smile.

"I have no interest in bloodplay," Castiel said, again in that careful tone.

"Did Sam tell you about that, or Dean?" Ruby asked, actually curious.

"Dean's lent me the use of his laptop," Castiel said. He leaned back on the hood and looked up at the stars. "It's been--edifying."

"Did you find God on googlemaps?" Ruby asked.

Castiel's eyes were sharp, immediately present and unhappy. "Don't jest about my Father."

"Who said I was kidding?" Ruby said, but she knew well enough to drop that line of questioning. Ruby knew firsthand that answers never came that easy.

The night air was cool against her skin, and a wind eased in from the south. Three cars passed the road that connected with the parking lot--one had a headlight out. A lone cricket chirped an unsteady song, and though Ruby thought the cold couldn't kill it fast enough, Castiel had his head tilted slightly like he was listening with secret pleasure. Excruciatingly bored and almost willing to risk a smiting, Ruby said, "You could always ask Dean."

"About God?" and oh, Castiel was almost cute when he was all confused like that, like a little baby pigeon that didn't know it was just another sky rat.

"About sex."

Castiel's eyes went wide. "You're not suggesting--"

"He'd go for it." Ruby paused and calculated risks. "Or completely shut you out and say he never wanted to see you again. Play your cards right, you could probably get both, one then the other."

"I think," Castiel said, voice faint like it was coming from far away, from whatever distant future held a Dean Winchester who either fucked or failed to keep his favorite angel, "that I will take you up on your offer."

"Awesome," Ruby said, jumping off the car. "We can use the backseat."

The thought of Dean's face at discovering Ruby desecrating Impala and angel in one go was even sweeter than the two hours and three orgasms that followed after.

 

2\. The Mark: Dean Winchester, Angry, Broken, and Her Boyfriend's Brother

It wasn't as much hate sex as she'd expected. One moment he had her pinned to the wall, tearing at her shirt to get at her breasts, loose threads releasing plastic buttons to decorate the cheap, dark motel carpet; the next, he was crying into her neck, silent and wet and broken. She hadn't anticipated this stage until at least a few weeks into their fucking, but never let it be said Ruby wasn't adaptable. She rubbed a hand against the back of his neck, stirring the short hairs of his hairline with her fingertips and scratching very gently with the tips of her nails. "Sh," she said, walking him back toward the bed.

"I don't--" Dean choked out, and Ruby repeated, "Sh."

Then, "You need this right now." She didn't say _Trust me_, but she did say, "I've got this," as she undid his plaid over-shirt button by button by touch alone, mouthing at his jawline and tracing the rasp of his stubble with her tongue. When she pulled back, he had his eyes closed, and she was okay with that, because he was helping pull off his white under-shirt, went down easy under her hands, sprawled out like a feast for the eyes on the garish green bedspread. When she pulled off his belt, he made another choked, horrible sound, and Ruby crawled over him to bite his chin, bring him back from wherever he was attempting to retreat, to hide. The denim of his jeans was rough and folded back to reveal soft cotton boxers.

"Did you know," Ruby said almost conversationally, dragging her fingers through the coarse hair above Dean's dick, "that Alastair and I had met before?" The sound Dean made this time was almost worse, and Ruby brought her hand back up Dean's stomach to his chest, flicked one nipple experimentally. "You and John Winchester were something of a bonus for the rest of us. Before that his--attentions--were spread between those on the rack and any demon he could catch equally. I doubt he'd remember the rest of us, but even one night--" Ruby trailed off and pulled Dean's head up for a biting kiss.

"Ruby," Dean said when she moved on to kiss the corner of his jaw, then his earlobe, before pulling it into her mouth. "Just--shut up. Please."

It was the please that did it for Ruby, and she canted her hips against Dean's, searching for any spark of friction. Dean's hands were desperate against her hips again, and he pulled at her jeans until they were sliding down her thighs. Backing off to step out of them would have been easier, but Ruby enjoyed watching Dean's expression at her contortions to rid herself of them without leaving the comfort of the bed. As she tossed the jeans into the corner of the room, Dean moved backward until his back hit the headboard. Ruby followed, and Dean pulled her back against him, into his lap; he didn't bother tugging down her panties, just pushed the cloth aside to press his fingers against her, into her, searching with expert precision for that place deep inside where the pressure was most needed. Ruby arched her back and said, "We all come out of Hell broken, Dean. That's the entire point."

Dean slumped against her, resting his face against her chest, and he mouthed at her right nipple through the thin fabric of her bra. "Do you really think now is the time for talk therapy?" Dean asked.

"Do you really think this is about therapy?" Ruby returned.

Dean huffed out a bitter laugh, and Ruby shivered at the warm air against the wet spot his mouth had left behind. "You're right, we're doing this because we like each other so goddamn much."

Dean hadn't let up the rhythm of his fingers, and Ruby made a happy sound as she trailed a hand along Dean's collarbone. "There's only one thing you're wrong about, Dean." Her smile was bright like a razor catching the sun in its downward arc as she pressed Dean against the mattress, pulling his fingers away to replace with his dick. Dean made a sound of pleasure so sharp it was almost pain. "I _do_ like you."

That didn't stop her from wringing two orgasms from him and then leaving immediately after to see Sam. It wasn't like Dean actually _wanted_ her to stick around and watch him cry into his pillow, anyway, and he would figure out on his own that this wouldn't fuck things up with his brother--eventually. Until then, his pain was not only delicious, but useful. Guilt would drive him to call Sam and apologize for being an ass and letting him go, and anger would, as ever, drive him forward and keep him from caving on the whole "Michael Sword" issue. Ruby didn't intend either of her boys to be worn by (former) archangels to prom. For one thing, they would clash with _everything_.

Ruby liked Dean, but more importantly than that, she had a use for him. All that separated her from everyone else was that she was also getting sex in the bargain. In this way, Ruby's life was, to be honest, pretty damn awesome.

 

3\. The Mark: Jo, One Seriously Hot Hunter

"This could be our last night on Earth," Ruby said. "Or yours, anyway; I can always pick up a new host."

"Does this really work for you?" Jo asked disbelievingly.

Ruby shrugged and smiled shamelessly. "Always worth a shot. And it gives you practice for your 'I have self-respect' speech for when Dean finally works up the nerve to slink over and use the same line."

Jo looked over at Dean, who was staring at Ruby with no little amount of suspicion, then she turned back to Ruby, who made sure to put on her most dazzling smile.

"Fuck it," Jo said, gripping Ruby by the upper arm. "Let's go before I change my mind."

"How romantic," Ruby said. "With charm like that, I see how you get all the girls."

"What did I say about changing my mind?" Jo said, dragging her for the stairwell.

Ruby glanced back at Dean's look of sudden horror and Sam's resignation--_sorry, Sam, but I left you Dean!_ Ruby thought--and grinned ever the more fiercely.

When they made it up to Jo's room, she turned like she was maybe having second thoughts, and Ruby pressed forward, bore her back against the door and pressed persuasive kisses to that lush mouth. Jo's lips parted, and Ruby licked them, darted her tongue in for the briefest of touches before pulling away again, repeating this dance in a series of insistent, teasing kisses. When Jo began to give chase, to follow Ruby's mouth and tongue with her own, Ruby took a full step back and asked, "Aren't you going to invite me in?"

Jo slumped against the door, banging her head gently. She looked up as if imploring the world for strength. "Yes, Ruby," she said after a moment. "Would you like to come in?"

"Very much," Ruby said, placing her hands on Jo's hips and sliding her palms up and under Jo's shirt. Her skin was smooth and warm against Ruby's fingers; Jo was a competent and driven hunter, but she also apparently took the time to moisturize. Ruby expressed her approval with a series of soft kisses trailing down Jo's neck before sucking at the join between neck and shoulder.

There was the thud of Jo's head hitting the door again, then, "Inside? Now?"

"Absolutely," Ruby said at the time, and she remembered that invitation hours later, watching Jo bleed out before her very eyes, offering to not even wait that long before blowing up both herself and the building to buy them all a little more time.

"Fuck that," Ruby said, and damn it, she _liked_ this body, but she could always find a new one, whereas Jo could do things with her tongue that had to be experienced to be believed. "We can set a timer." Ruby waltzed right in without waiting to be asked, much less a repeat invitation.

It had been a while since Ruby had to hold a host together like that, and she'd never really done so for the purpose of actually keeping the host kicking long enough to get her into the ER, but it was totally worth it when, a month and a half later, in a new coma girl body (red was in this season), Jo welcomed her back into town with that same incredibly talented tongue.

"Want to give her a spin?" Ruby asked, twirling obligingly for Jo's perusal.

"You drive," Jo said, and she looked good, so much better than when she'd been bleached out and pale under the hospital lights, but dark shadows still graced her under-eyes. "I'm tired and technically still recovering."

"Maybe we should wait," Ruby said, stepping back with a teasing smirk.

"I'm not that tired," Jo said. With a hint of humor and a dark smile, "This could be our last night on Earth. Or mine, anyway; you could always pick up a new host."

Jo, Ruby thought as she pulled her in for another excellent kiss, was definitely Ruby's kind of girl.

 

4\. The Mark: Amelia Novak:

"I'm sorry for your loss," Castiel said in that alien robot voice he used when he was trying to be compassionate and hadn't quite gotten enough coaching from Sam.

"I'd already lost him," Amelia said, and her smile was bitter. "It was just a matter of acknowledging it."

"You know what would make you feel better?" Ruby asked, sidling closer.

"No," Sam said, in his _I can't believe we're about to have this conversation_ voice. "I don't think that would make her feel better."

Amelia looked Ruby up and down, and Ruby was _so_ in. "I don't know," Amelia said. "I'd like to hear her out."

"I don't believe this would actually be beneficial," Castiel said, and he was Ruby's new best friend and favorite wing man, because Amelia's back went stiff, and her glare was fierce as she said, "I don't believe it's any of your business."

"Seriously?" Sam demanded of Ruby, then turned to Dean as if to ask for help.

Dean held up his hands and said, "Whoa, if you think I'm getting involved, you are so far off target as to be in another freaking _timezone_."

"You can be involved if you'd like," Ruby said, because though she didn't expect anyone would go for it, she still had to make the effort.

"No," Amelia said, stepping forward. She flicked her eyes up and down Ruby's form again, and Ruby was pleased at Amelia's appreciation of Ruby's good taste. "I'm done with men, and if we're going to do this, we'll go by my rules."

Ruby wondered what Jo was doing and if she was close enough to drop by in the next few hours. She wondered if she could talk Jo into it at all. Something to think on for the next time. Ruby smiled winningly and said, "I don't mind letting you drive."

Of course, this proved to be something of a disaster when it turned out Amelia didn't know what the fuck she was doing.

"Was Jimmy this bad at sex, or is it the new to women thing?" Ruby had to ask. "Because really, in theory this body's not all that different from yours. I have a few different kinks and sweet spots, but we're operating on the same basic principle."

Humiliation (or was that suppressed rage?) turned Amelia a delightful flushed rose that extended all the way to her breasts.

"Never mind," Ruby said. "I think I've found something that works for me."

It turned out Ruby was going to get her hate sex after all. Amelia left marks that lasted for _days_.

 

1\. The Prince: Sam Winchester, Surprisingly Decent Boyfriend

Sam licked every mark Amelia and others left on her, pressed his lips to the bruises and burst blood vessels, imprinted his own teeth over any shadows others left behind as if relearning her skin with his mouth alone. He said, "I don't really need to know details about the wonders of Jo's tongue," and dropped Ruby off at the front door, then picked her up the next day and pulled her in, breathed deep Jo's almond body wash and pear shampoo and Ruby's own spicy scent underneath, and when he said, "I convinced Dean to let us go to Disneyland," Ruby knew it wasn't out of jealousy or one-upmanship, but because Ruby had mentioned offhand the other day that she'd never been. When she told him, "You know I'm fucking Dean, right?" Sam answered only, "You know that's not going to last when he finally gives in and admits his thing for Cas, right?" in a tone that said he knew she knew, but wanted to let her down easy anyway.

It wasn't a discontent, dissonant thing between them, her age, her flings, the way she let it seem she held Dean just as dear. Even the demon blood thing was a hurdle they overcame eventually when she'd smiled and shrugged and said, "I told you it was just a feather. You don't need it, Sam," before she held his hair back off his forehead so he could vomit in the basin again.

It wasn't discontent or dissonant, but it _was_ a thing, and staring down at Sam's sleeping form, Ruby murmured, allowed herself to be sappy where only she could hear, "You know I'll always come back for you, right?" and, "You're almost better than French fries," and, "If you don't want to be the boy king, I'll find another way. I've _got_ this."

Dean and Heaven might have angels of the Lord, and Hell might have its fallen angels, but Ruby was the best fucking demon there was. Ruby leaned down and brushed her lips against Sam's temple. "I promise," Ruby said, and she was the kind of old school witch who kept the promises she'd sealed with a kiss.

(Besides, it would take her decades to find and train someone of Sam's potential again.)


End file.
